The alienation of the Geraldine earls of Desmond was guaranteed by the execution of Earl Thomas at Drogheda in 1468, but it was compounded by internal struggle over the succession to the earldom. King Richard, who succeeded his brother Edward IV in 1483, put out feelers to James FitzThomas, successor to Thomas Earl of Desmond executed at Drogheda, by means of a letter delivered by the Bishop of Annaghdown. In the letter Richard offered to choose a suitable wife for the new earl if only he would abandon his violence and adopt English ways. He sent him a collar of gold with the King’s insignia, presumably the Yorkist emblem of the boar. The letter is preserved in the King’s published correspondence. It proved all to no avail. Earl James was murdered at Rathkeale at the end of 1487. By then King Richard had been succeeded by Henry VII, the first of the Tudors, and the next earl, Maurice the Lame, welcomed the Yorkist pretender Perkin Warbeck and assisted his campaigns of 1491-97 to dethrone Henry.
The most dangerous of the earls was probably James (1520-29), a grandson of Thomas of Drogheda. We are now in the reign of Henry VIII. Earl James received the envoys of the Emperor Charles V (simultaneously King of Spain) at Dingle in 1529. Unfortunately, the new Earl was equally dangerous to the hopes of the Desmonds themselves. No sooner succeeded to the earldom in 1520, he waged a fierce campaign against the Muskerry MacCarthys, so fierce that his own uncle (and successor), Thomas the Bald, took the side of the MacCarthys, defeating Earl James at Móin Mór (Mourne Abbey). James left no male heir, and a change in outlook in respect of foreign conspiracy and attitudes to the English government is apparent in Earl Thomas, who was a very old man when he succeeded, ruling from 1529 to 1534. Unfortunately, Thomas the Bald’s successor was murdered by his cousins, leading to a break in the rightful succession and the transfer of the earldom to James FitzJohn, father of the unfortunate last reigning Earl, Gerald or Garrett.